Dean of Students Jack Oros first came to Greenhill intending to be a math teacher. Little did he know that 35 years later his influence would have changed the lives of many students and faculty at the school. 

Oros interviewed for the position of an Algebra II teacher in 1989. On campus, he quickly became acclimated to the way that students and teachers at Greenhill had relationships he had rarely seen at other educational institutions.   

“It’s a special thing, and teachers that come here from some other places say it’s not like elsewhere,” Oros said. “Also, kids that come here from their other schools say they don’t get it for a while, until they eventually understand that the teachers are there for them.” 

Now, Oros has decided that it is time for him to retire after 12 years as Upper School dean of students. 

“When I retire, I’m going to miss having my hand in the middle of it all,” Oros said. “What am I going to do?”   

Policy and Tradition 

Throughout his time as dean, Oros has implemented a variety of policies and traditions. He says he hopes many of these will be carried on once he leaves. 

 “Our goal is keeping kids safe,” Oros said. “Breathalyzing before school dances was my idea.”   

 Before this was a policy, students showed up to school dances inebriated. This caused the dances to be not as enjoyable for the underclassmen, according to Oros. 

“We started the random breathalyzer and in doing so, it changed the culture of the dances,” Oros said.  

Others on campus, including Head of Upper School Trevor Worcester, have noticed his efforts to support the student body. 

“[Oros] pays attention to that bigger swath [of students], and I think that’s important for a [dean of students] to have that kind of pulse on what’s happening,” Worcester said. 

 Oros has also made various old traditions into his own. One of those is Bagel Tuesdays. 

“Through bagel days, he brightens everyone’s day and smiles at each student as he hands out the bagels,” said senior Brenna Norton, who is also one of 13 students in the Oros advisory.   

Although the tradition was started by his predecessor, Oros began making bagel chips out of the leftover bagels. In an added Oros touch, the flavors range from pizza to chocolate chip.  

“I don’t want to throw away old bagels, so I make chips out of them,” said Oros. “Those sell as popular or maybe even more than the bagels.” 

For many students and faculty, Oros’s traditions and policies have become synonymous with campus life.  

“Mr. Oros makes sure that our school environment is always a special place with his tradition and every rule and policy he has made has really helped us all grow,” sophomore Jackie Dishman said.  

Memories  

Throughout his time at Greenhill, Oros says he has collected many memories that he will cherish. 

One of these from early in his time at Greenhill was a faculty chili cook-off.  

“That was a fun experience because it was a time when all the faculty knew each other,” Oros said. “It was a much smaller team.” 

Another cherished experience was attending the Independent Schools Association of the Southwest Arts Festival almost every spring. 

“I loved all the ISAS’s I went to and watching our kids perform and all the art being displayed and then getting to see all the other schools,” Oros said.  “It’s a really special time and I wish more faculty could go.” 

 Oros has had an impact on student life as a math teacher and dean of students. Another area where Oros has made his mark is as a student advisor. He advised one student cohort that graduated in 2022, and another that is about to graduate.  

 Senior Max Kettles, who switched into the Oros advisory as a junior, cherishes this experience as well. 

 “The environment he fostered during advisory makes [students] excited for advisory each day,” Kettles said in an email. 

Oros says he realized it was time for him to retire when he had to decide at the end of last year whether to take on another cohort of students in an advisory capacity. 

Now, after 35 years at Greenhill and 44 years in education, Oros says that he is “pretty tired but excited to see where the school goes.” 

Legacy 

As Oros heads into his final days at Greenhill, he is filled with pride at what the school has become. 

“I always say we put out a good product,” Oros said. “I’m very proud of the kids that are graduates and the people they become in the world.” 

Already, community members are thinking about what will be lost with Oros’s departure. 

Worcester says one of the things he will miss is Oros’s “institutional knowledge.” This vast knowledge of Greenhill’s past has helped Worcester navigate his years at Greenhill as a teacher and administrator.   

“[Oros] deserves all the celebration and tribute you all are doing and everyone else is doing for him,” Worcester said. 

In considering how to replace Oros, administrators decided his vast responsibilities needed to be shared across two positions. 

“I mean, the fact that we’ve split his job into two roles says a lot,” Worcester said. 

Students say they are going to miss his smile in the hallway, or his drawer of candy that’s always open. 

 “Mr. Oros knows everyone’s name and always goes out of his way to make people feel welcome, which is something I’m really going to miss, especially in our senior year,” junior Ashley Weinstein said. 

More than anything, Oros says he will miss his connection with his students, and he will miss watching their growth throughout high school. 

“Greenhill kids are good kids deep in their heart,” Oros said. “Deep down inside, Greenhill kids are special kids.”